37464-83-8

Basic information

• Product Name: methyl 5-hydroxy-5-phenylpentanoate
• Synonyms: methyl 5-hydroxy-5-phenylpentanoate
• CAS NO: 37464-83-8
• Molecular Weight: 208.257
• Mol File: 37464-83-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 5-hydroxy-5-phenylpentanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-hydroxy-5-phenylpentanoate(37464-83-8)
• EPA Substance Registry System: methyl 5-hydroxy-5-phenylpentanoate(37464-83-8)

Safety Data

• Hazardous Substances Data: 37464-83-8(Hazardous Substances Data)

Upstream product

• 85636-50-6 1-(trimethylsiloxy)-1-methoxy-1,3-butadiene 
• 100-52-7 benzaldehyde 
• 72853-47-5 5-hydroxy-5-phenyl-pent-2-enoic acid methyl ester 
• 1501-04-8 Methyl 4-benzoylbutanoate 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 67-56-1 methanol 
• 335645-38-0 2-(3-chloropropyl)-2-ethoxy-1,3-dioxolane 
• 74900-27-9 1-(3-chloropropyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 

Downstream Products

• 10413-17-9 6-phenyltetrahydropyran-2-one 

Relevant articles and documents

Enzyme mediated kinetic resolution of δ-hydroxy-α,β-unsaturated esters as a route to optically active δ-lactones

A novel synthetic route to optically active saturated and unsaturated δ-lactones based on enzymatic kinetic resolution and ring-closing metathesis reactions has been proposed. The influence of temperature, co-solvent, organic additives and the substrate s

Masked ω-lithio ester enolates: Synthetic applications

The protocol of lithiation by means of lithium and a catalytic (5% molar) amount of DTBB (4,4'-di-tert-butylbiphenyl), applied to ω-chloro ortho ester 6 under Barbier-type conditions gives, after final acid-catalyzed methanolysis, the corresponding functionalized esters 8 or 9 (for chlorotrimethylsilane as electrophile) or, after ortho ester deprotection and acid catalyzed treatment, the δ-lactones 11. The procedure is also practical for bicyclic ortho esters 14: the β-chloro OBO ester derivate generates the γ-lactones 15 and the γ-chloro OBO ester gives corresponding esters 8.

Masked β-, γ- and δ-lithium ester enolates: Useful reagents in organic synthesis

The reaction of ω-chloro orthoesters 1 with lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5% molar) in the presence of different electrophiles [ButCHO, PhCHO, (CH2)5CO, Et2CO, PhCOMe, PhCH=NPh, Me3SiCl] in THF at -78°C leads, after hydrolysis and acid-catalysed methanolysis, to functionalised methyl esters 2. In the case of chlorotrimethylsilane, hydroxyethyl esters 2′ are isolated. The reaction is also applied to bicyclic orthoesters 3: whereas β-chloro derivatives and carbonyl compounds gives directly γ-lactones 4 after hydrolysis, the corresponding γ-chloro derivative affords the expected methyl esters after methanolysis.